When to hire the first employee

Let me start by setting the scene:

• We’re entirely bootstrapped (self-funded and no outside money)
• The MRR doesn’t cover our fixed costs yet
• I have way too much on my plate (like any other entrepreneur, but still)

A year ago, I could go three days a week without any meetings, sometimes just having one or two meetings in a whole week.

Since the beginning of August this year, I’ve had (on average) 3.5 online meetings per day, the vast majority with potential customers.

On top of that, there is all the back office and follow-up work related to customer meetings, so in reality, I spend 1.5 to two hours per 45-minute meeting.

Let me start by saying that this is a “luxury problem,” and I’m not complaining. Many entrepreneurs would kill to have so many customer meetings, and I’m super happy I do. However, you can only be in one place at a time, and when I’m spending most of my time on sales and onboarding meetings, I’m not working on our product.

And that sparked the thinking: Is now the time to bring on a colleague?

A whole new world

Thinking about what it would mean and take to bring an FTE (full-time employee) onto Herodesk made me feel like John from Pocahontas, who’s discovering a whole new world (the song is from Aladin, I know, but I feel more like John than Princess Jasmine).

The issue of time is clear. There are two buckets of tasks that each can fill a full-time position: sales/onboarding and product development.

I need an extra set of hands to help me with one of them. I’m highly motivated by product development—that’s what I think is funny and what I believe I’m best at—so I’d like to bring on someone to help with the customer-related tasks.

It’s the economy, stupid!

Our MRR (monthly recurring revenue) is currently at €3.280. From launch, it took 7mo and 14d to reach €1.000. Then it took another 2mo and 22d to reach €2.000. Another 2mo and 0d to reach €3.000 – and in September, we’ve grown the MRR more than 28% compared to August 31st.

But it still doesn’t take a genius to see that €3k MRR isn’t enough to support the business with two full-time employees (plus everything else).

However, MRR != Cashflow. Many customers pay yearly upfront, so our cash flow is almost double the MRR.

You don’t wanna fuck this (the finances of your business) up, so I’ve spent a lot of time with our accountants and laid out 2025 budgets, cash flow analysis, etc.

As a brilliant man once told me (you know who you are):

When it comes to budgets and forecasts, the only thing you can count on is this: You can never actually count on them.

Still, we’ve laid out a plan that has forecasts, estimates, uncertainties and everything else that an entrepreneurial business plan with financial projections has – and I’m confident that it’ll hold.

I don’t wanna bring on an FTE and risk tanking the business because things are starting to move faster, and the real learning I wanna pass on (from this and especially previous experiences) is this: Cash is king. Make sure there’s enough to pay the bills every month, because if you don’t, it’s game over.

Culture eats strategy for breakfast

Who are “we”, when “we” is suddenly a group of people that includes others than me?

With the finances in place, I’ve started to think a lot about what kind of business I want to build.

• What do we value?
• How do we work?
• All that stuff…

A lot of it will (and should) develop over time as the business and the number of people in it grow, but I’ve still done some thinking about the foundation. A lot of it is essentially an experiment because I’ve never tried it before, but I like the ideas and how I hope it’ll play out in real life.

• We’re going to work fully remote (no office) and meet up in-person ~3 times per year.
• We should value focus time to get shit done and avoid unnecessary interruptions (no, we’re not gonna use Slack).
• We should prioritize data-based decisions above veto’s and gut-feelings, ownership and accountability above confirmation, agility and iterations above extensive planning, and openness and discussions above status and defensiveness.
• We aim to reach our goals as a team and prioritize long-term success over short-term wins.

I’m gonna write a lot more about this in the future, but I hope it gives you an idea of what I’ve been thinking about going into this, transforming Herodesk from a one-man-band to an organization with multiple employees.

I strongly believe that you have to think about these things when you start hiring; otherwise, I fear things can go south quickly.

So, when is the right time?

You can’t give a universal answer to that question. It depends.

But for me, the answer is: Now!

Yesterday we opened a new position for a full-time customer success manager at Herodesk: https://herodesk.io/da/jobs

I’m so excited to take this next step on the journey and am confident that bringing on the right CSM will take the whole company to the next level.

Please share this with your network and if you know anyone who might be interested. The link above has all the details about the job 🙏